78469-76-8Relevant academic research and scientific papers
Total synthesis of (+)-colletodiol from (S,S)-tartrate and (R)-3-hydroxybutanoate
Schnurrenberger, Peter,Hungerbuehler, Ernst,Seebach, Dieter
, p. 733 - 744 (2007/10/02)
The macrodiolide antibiotic (+)-colletodiol (7, Scheme 1) was synthesised.The configuration was thus proven to be (6R,11R,12R,14R). - Key intermediates (Schemes 9 and 10) are the two hydroxy acids 43 and 64, which were prepared from dimethyl (S,S)-tartrate in 20percent overall yield (12 steps) and from (R)-3-hydroxybutanoate in 57percent overall yield (6 steps), respectively.The two hydroxy acids were cyclised to give, after deprotection, the title compound. - Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.
Chiral Electrophilic Synthetic Building Blocks with Four Different Functional Groups from Tartaric Acid, 2,3- and 3,4-Epoxy-butanediol Derivatives in All Four Stereoisomeric Forms
Hungerbuehler, Ernst,Seebach, Dieter
, p. 687 - 702 (2007/10/02)
Efficient and simple procedures have been developed for the preparation of the threo- and erythro-3,4-epoxy-1,2-butanediol derivatives 7 and 9 in both enantiomeric forms from tartaric acid.These epoxides should prove versatile as alkylating reagents in sy
